Chalcone glycosides isolated from aerial parts of Brassica rapa L. 'hidabeni' suppress antigen-stimulated degranulation in rat basophilic leukemia RBL-2H3 cells

Bioorg Med Chem. 2010 Oct 1;18(19):7052-7. doi: 10.1016/j.bmc.2010.08.008. Epub 2010 Aug 9.

Abstract

We isolated three chalcone glycosides along with other glycoside constituents from the aerial parts of Brassica rapa L. 'hidabeni' and examined the effects of these compounds on the antigen-stimulated degranulation in rat basophilic leukemia RBL-2H3 cells. Treatments with both 4'-O-β-D-glucopyranosyl-4-hydroxy-3'-methoxychalcone (C1) and 4'-O-β-D-glucopyranosyl-3',4-dimethoxychalcone (C2) markedly inhibited antigen (Ag)-stimulated degranulation. To gain further insight into the inhibitory mechanisms by C1 and C2, we examined early intracellular signaling events, Ca(2+) mobilization and intracellular reactive oxygen species (ROS) production. Both C1 and C2 did not affect early intracellular signaling events but exhibited the suppression of intracellular ROS production through NADPH oxidase (NOX) inactivation. From these results, we proposed that the inhibitory effects of C1 and C2 on Ag-stimulated degranulation were mainly due to suppression of intracellular Ca(2+) elevation by suppression of intracellular ROS production through NOX inactivation. Our findings suggest that C1 and C2 would be beneficial to alleviate symptoms of type I allergy.

MeSH terms

  • Animals
  • Antigens / drug effects*
  • Antigens / immunology
  • Biphenyl Compounds / pharmacology
  • Brassica rapa / chemistry*
  • Cell Degranulation / drug effects*
  • Cell Degranulation / immunology
  • Cell Proliferation / drug effects
  • Chalcones / chemistry
  • Chalcones / isolation & purification
  • Chalcones / pharmacology*
  • Drug Screening Assays, Antitumor
  • Free Radical Scavengers / pharmacology
  • Glycosides / chemistry
  • Glycosides / isolation & purification
  • Glycosides / pharmacology*
  • NADPH Oxidases / antagonists & inhibitors
  • NADPH Oxidases / metabolism
  • Picrates / pharmacology
  • Plant Extracts / chemistry
  • Plant Extracts / isolation & purification
  • Plant Extracts / pharmacology*
  • Rats
  • Reactive Oxygen Species / analysis
  • Reactive Oxygen Species / metabolism
  • Structure-Activity Relationship
  • Tumor Cells, Cultured

Substances

  • Antigens
  • Biphenyl Compounds
  • Chalcones
  • Free Radical Scavengers
  • Glycosides
  • Picrates
  • Plant Extracts
  • Reactive Oxygen Species
  • 1,1-diphenyl-2-picrylhydrazyl
  • NADPH Oxidases